Caught And Conditioned 3 free porn video

The standard disclaimer applies: If you are under the age of consent in your area please continue no further, go find some place more age appropriate, there will be plenty of time for this when you are older. If you are of legal age and any or all of these themes: humiliation, crossdressing, punishment, non-consensual sex, and/or possible homosexual themes bother you please read no further. However, if this disclaimer has peaked your more prurient interests please enjoy some, hopefully one handed, reading! :-)~ (Wink, wink, nudge, nudge, knowing look) Caught and Conditioned (Part 3) With everyone well fed I took my sweet time getting the dishes done and things put away. All too soon though my work was done and the inevitable loomed large. "Let's go!" shouted Gail. "Time for the show," added Tammy. I slowly made my way to the TV room where they were all lounging watching a DVD of "The Rocky Horror Picture Show". Gail fumbled with the remote for a moment and then said "I think you should go along with Frankie on his intro number. (For those of you who don't know the movie Dr. Frank N Furter is a "Sweet transvestite from transsexual Transylvania" and his introduction to the audience is a strutting musical number, in lingerie, singing "Sweet Transvestite." I cringed at the thought and glanced at Eric, hoping in vain for some help, only to see a lusty smile and a hand gently rubbing the growing bulge in his shorts. Once I was suitably attired, thus stripped to my lingerie, the DVD was restarted at the proper point and I had to strut and sing along with the video of Tim Curry. Unfortunately I was unconvincing and it took four complete run thrus of the song before the audience was sufficiently satisfied that I was in fact a sweet transvestite. Gail then fast forwarded to a song where Frankie sings about making you a man. She explained that while this song was playing I was to help make Eric. As usual she was more amused with her 'wit' than anyone else was, but this never seemed to bother her. After Gail gave me detailed instruction about my upcoming performance the video was again started and my further debasement was underway. I followed Gail's instructions and strutted up to Eric and dropped to my knees. At this point he was wearing only some white socks, a t-shirt, shorts, and underwear. I slid my hand up his left leg and back down sliding off his sock and then lifting his foot to my face kissing the sole and then red faced I repeated this with his other foot. Once this was done I bent forward and slid my tongue up his leg from the ankle to his crotch and then repeated the same with his other leg, pausing to blow warm breath through the front of his shorts. Eric let out a little groan as I slid closer reaching out and pulling his shirt over his head and then gently nibbling each of his erect nipples. I then trailed down his stomach to his navel where I lingered slightly with my tongue before again blow several puffs of warm air into his shorts. Again Eric groaned and this time shifted his weight, lifting his hips cueing me to remove his shorts. I followed my instructions and did just that being careful to leave his tighty whities in place. The front of his underwear bugled obscenely with his excitement and his breathing quickened slightly. I glanced up to see his eyes fixed on me as he anticipated his ensuing pleasure. I felt the heat in my cheeks as I again blew into his crotch and saw is manhood twitch. I thought of what I was about to do, again, and the audience and though it seemed unbearable I knew I might better suffer this shame than to become an internet star. I was brought back from my thoughts by a sharp smack on my upturned rear by Tammy. "The show must go on," quipped Dina. I hesitated for a second and then leaned forward and rubbed and licked the bugle in front of me with my nose and tongue as Gail had previously instructed. Eric, eager as always thrust his hips forward into my face increasing the pressure on this engorged rod. I drew back slightly and saw a wet spot forming at the tip and steeling myself I leaned forward and again began to lick at his fabric encased cock concentrating on that wet spot. As I worked him closer and closer to the peak of his excitement the front of his briefs became more and more transparent with the combination of his precum and my saliva. I did my best to imagine that I were somewhere else and not doing what I was doing, but it was difficult with Eric's moans and insistent thrusting, as well as, the banter from the girls. Just as he was about to spill over the edge I felt a hand tap me on the back. This was Gail's prearranged signal to stop momentarily. As I paused and moved my head back Eric gasped in desperation at his pleasure delayed. The look of confusion on his face gave way to one of recognition and lust as I reached up and hooked my fingers into his waistband. He quickly lifted his hips and I slid his briefs free. There I knelt between his wide spread thighs, him totally nude, me dressed in lingerie, and all under the watchful eye of my three tormentors and now, I noticed, a video camera! I hesitated briefly looking from the camera held by Tammy to my unyielding step-sister and then as a single tear rolled down my cheek I returned to my task taking a long lick up Eric's shaft before engulfing the glistening head. With the girls all there for an audience that was all it took. I felt the head pulse and tried to pull away, but was prevented by the handful of my wig Eric had a firm grip on. Soon he shuddered and thrust into the back of my throat as pulse after pulse of thick goo ran down my throat. I managed to swallow most of it without choking and the girls made note of the 'willingness' with which I swallowed. Several minutes passed as they discussed my performance as I sat humiliated on floor and then Gail announced that it was too quick and I needed a repeat performance as the training portion was non-existent as I had done too good a job. I tried to protest, but per usual it went virtually unheard, so about 20 minutes later I again found myself kneeling between Eric's legs with his cock pistoning in and out of my mouth. "Nibble his balls." "Suck his balls." "Lick the shaft." "Deep throat him." And finally, "Tongue his ass." This request seemed to cause the world to pause as all eyes turned toward Gail. "What? You heard me you little sissy, if you can lick our asses you can do the same for your boyfriend!" barked Gail. Eric looked at me and then shrugged and slid his ass off the edge of the couch and then lifted his legs high in the air so that his wrinkled pucker was in full view. The next command of, "Get to it," by Gail was punctuated by a sharp crack to my behind with a belt I yelped and moved to the task at hand. I reached out with my tongue and was happy to find Eric was freshly showered as there was almost no taste other than a light musk of his sweat. Of course never satisfied Gail pushed me forward to full penetration which I resisted until the 4th or 5th lash from the belt and then I relented as to the cheers of my three evil mistresses and the moans and groans of my now 'boyfriend'. Finally, after what seemed like forever I was allowed to return to the rock hard cock and the series of instructions until finally I was swallowing yet another load. I sat back exhausted the acrid taste in my mouth, my jaw aching, my ass burning, and more ashamed and humiliated than I ever would have thought possible a few weeks before. My rest didn't last long and some I was wearing nothing other than a garter, heals, stockings, and an apron and helping Eric settle into my room before going about my other chores. It soon became obvious it was no longer my room as anything Eric didn't like was packed away in the closest and his stuff was put in its place. It wasn't a lot of stuff, but even just a couple posters etc seemed like a lot after everything I had been through. Looking back I'm sure this was another ploy by Gail to break me down even further and I hate to admit it worked. The rest of my day was pretty 'normal' with me cleaning, do laundry, and cooking. The big difference was that not only did I have three mistresses to wait on hand and foot I now had a master. Eric took great pride in ordering me around, rubbing against my ass with his cock while I was working, and pinching and fondling it as well. I served dinner and when everyone was finally waited on sufficiently I sat in my designated place next to Eric. I soon found that meals were going to be even more distressing. Not only would I be judged and punished on my cooking and service, but now I would be constantly groped throughout the meal. The girls giggled and asked mocking questions as I struggled to maintain a calm demeanor as Eric's hands roamed over my legs and ass. After dinner each of the girls decided to pull me into their bedroom for some oral service before the night was over and in between I fetched drinks and snacks and performed a few other humiliating tasks such as sucking toes etc. Finally, the day drew to a close and to my surprise everyone saw me to my or should I say Eric's room. I was instructed to strip completely and was given a very sheer nightie and nothing else to wear. In the mean time Eric stripped to his briefs and slid into bed and then pulled back the covers and patted my side. The girls looked at me expectantly as I slide in next to him and he cuddled up next to me. "Don't be shy baby. Everyone knows you love the cock," he said paraphrasing a well known movie. The girls laughed as they headed for the door. "You two have fun now," laughed Gail. "Oh, we will," was Eric's response as he tossed his underwear across the room to show everyone he was now nude. The girls closed the door behind them as I felt Eric rub his rapidly hardening cock against my leg. "So are we going to go all the way tonight?" he asked. "What! Are you nuts I'm forced to get you off, but there is no way in hell that you are going to fuck me! I can't even believe you want to knowing that I'm a guy!" "Guy, girl whatever you look like a chick, you smell like a chick, you feel like a chick," he said running his hand down my smooth leg. "And best of all you suck dick like a chick." He paused and then added, "Eh, suit yourself, if you like the taste that much get to it!" he said throwing the covers aside. "And why should I?" "One: Because of a certain website, Two: Because I'm not letting you alone until you do, and Three: Because Gail told me to tell her if you weren't cooperative and that would mean another punishment, like another week," he said grinning. What I didn't know was that last part was a bluff, but a good one. Also, the website alone would have been enough incentive to debase myself yet again. The other thing that neither Eric nor I knew was that the girls now had two hidden video cameras set up recording all the action in the room from even more blackmail leverage. It wasn't long before Eric was groaning and splashing the back of my throat with his load. He made sure that I swallowed and then rolled over to go to sleep. Of course, sleep meant waking up at 2:00 AM and again at 4:00 AM for a repeat performance. The next morning brought at least some good news, for my secret anyway. Doug, Tom, and Jay had all been offered jobs working for Tom's uncle for the rest of the summer in Nebraska and they were flying out in the afternoon. I stayed hidden, unfortunately with Eric, until they headed to the airport. Tammy drove them all while I performed cleanup duties on Gail and Dina. Tammy returned and the girls decided that I needed to start working on my punishments for the 'boys'. Dina said she thought Tom would be a little angry but, mostly flattered that I used her for fantasy material and that she had an idea for my personal release on Sunday. The week continued much as the previous two, but with the boyfriends gone and apparently Marco off to other venues, my tongue was in even higher demand. My only break in this was towards the end of the week Gail got her 'monthly visitor' so I was off the hook other than her making service her ass a couple times just to maintain her dominance. The other big change was Eric's constant and demanding presence. In the 'privacy' of the bedroom he became more demanding and treated me in more demeaning ways. He called me bitch, whore slut, etc and was constantly slapping and pinching my ass. He loved having me lick his ass and suck his toes just to humiliate me. I wanted so much to rebel but, thoughts of the website and the warning that Gail had told him to report any disobedience kept me barely in check. Saturday morning was one small victory in the hell that had become my life. Over breakfast the subject that there were cameras in the bedroom that Eric and I shared was brought up by Dina. I was shocked but, it was Eric that should have been the one worried. Instead he bragged, "So you've been watching me put the bitch in here place?" "Yes we have," came the cold reply by Tammy. Eric wasn't completely stupid and now shut his mouth but, it was too late his cockiness was the final straw. "Yes, you seem to need some lessons in how to treat and talk about women," said Gail. "Now wait a second. She...er...he's no female," pleaded Eric knowing he might be in deep shit. "It seems you aren't even sure and it doesn't really matter because you need to learn your place. You may be above the little slut Stephanie in the pecking order but, that doesn't make you God's gift to women or give you the right to treat her like complete shit all the time," stated Dina. "So..." Gail said grabbing Eric. Soon he was struggling and losing against the three females and failing badly as he was being dragged toward the master bath. "Coming to help?" asked Dina turning and raising an eyebrow at me. "I thought you'd never ask I said," grinning ear to ear. I might not ever get a chance like this to inflict some of my torment back on one of my tormentors I thought as I bounded after girls and their flailing captive. As soon as, I grabbed his legs he pretty much gave up and resigned himself to his fate. Once in the bathroom Eric was given the full feminine treatment that I had been give with the exception of the fake breasts and wig. His face went ashen when the latex vagina was produced and glued into place and he nearly fainted when he was told it 'might' be removed the following Sunday if he learned his lessons well. He wasn't dressed as a girl but, more a sissy as he was required to wear lingerie (sharing my new collection), female shorts, tank tops, and around the pool bikini bottoms. Along with that he was required to have light makeup and his hair fixed in a slightly feminine manner. I swear he was more embarrassed like this than I was in drag. Once his look was set for the week then ground rules were discussed. I sat quietly watching Eric fuss in his pink short shorts and belly shirt with "Princess," on the chest in glitter. I had seen the shirt in the pile of clothes from the thrift store and had been horrified at it's implications but, for now I was glad they had bought it. The girls were deciding Eric's rules for the week and I loved it. "I think he should help Stephie with all her duties," said Tammy. "Except in the bedroom," added Gail. "Agreed," they said in unison and then they giggled. "I think he needs to learn to be a gentle lover and pay attention to foreplay," said Dina grinning widely. "Agreed," said Gail, "and Stephanie can be his practice partner. What do you think two no three hours a day?" "Oh my god," giggled Tammy, "that will be fun to watch." "And the added bonus is they will both hate it as their little peckers will be trying to get hard the entire time. Oh..." Gail said turning to look at me. "You will be doing the same with him so you both learn something. Not that I ever expect you to get a girl but, some of the same things work on boys." The girls then started to add the details of what they want to see. "We want to see lots of kissing." "Nibbling" "Sucking" "Fondling" "And this means everywhere on the body, ears, necks, nipples, thighs, feet, buttocks, and especially anuses," commanded Gail obviously amused with herself. The foreplay lessons were decided to take place in three 30 minute sessions after each meal, once the table was cleared and dishes done of course, and 90 minutes at bedtime. The girls decided that would be all for now but, depending on his behavior Eric's rules might be modified throughout the week. It was instantly obvious that Eric was going to have a painful week as every time one of the girls brushed against him he winced as his cock tried to expand in its latex prison. The morning was spent my the pool and I was given a break from waitress duties as "Little Eric," was put to work getting snacks and drinks etc in his pink string bikini bottom. As I watched him amused at his blushing cowed manner I also cringed thinking about the tan lines that were ever darkening from my own bikini. Lunch was prepared and served in tandem by Eric and me but, it also became obvious that this week was going to be very trying for both of us as we were expected to be hyper polite to one another. We had to thank each other for every little thing. Then Gail of course decided that each thank you should be accompanied by a kiss. So, when Eric hand me the mayo I thanked him sweetly and gave him a peck on the cheek. "No, no, no that will never do. A peck on the cheeks is appropriate for friends and family but, you two are lovers now. It should be on the mouth, open mouth and you better look like you mean it," instructed Gail. Now Eric and I both blushed crimson as I once again thanked him and gave him an enthusiastic, looking, open mouthed kiss. This was followed by about a half dozen or so more before lunch was on the table. During lunch there were several thank yous exchanged between us as items were passed but, it was decided that after each meal in addition to our foreplay lessons we would French kiss for ten minutes to warm us up. Eric and I exchanged a quick look of utter helplessness as this was announced. Eric knew it was hopeless to resist as the girls already had numerous pictures of his transformation and his new look, as well as, video from our bedroom. Eric and I tried to drag out the post meal cleanup as long as possible but, soon we were done and summoned to the living room. "Strip both of you," Gail ordered. As we started to disrobe she continued. "For the next week after every meal cleanup you will both come into the living room strip naked and set this timer to ten minutes," she said holding up a kitchen timer "and then lay on the floor together and French kiss passionately. Once the timer sounds you will reset the timer to 30 minutes and begin your foreplay lessons. This will all take place without being told and with enthusiasm! If you fail to do so times may be extended and/or other punishments may ensue. I'm sure Dina and Tammy and I can think of some interesting props to add to the lessons. I know I can," Gail said with that same evil look that always made me give a little shiver. Tammy and Dina were sitting on the couch and Gail took her spot in the recliner as we finished undressing and dropped to our knees facing one another. I gave Eric a nod and he reached over and started the timer and we began to kiss. I felt his tongue probe my mouth and I closed my eyes trying to pretend it was a girl I was kissing as our tongues played one against the other. "Eyes open sissies," ordered Gail. "You aren't getting off that easy pretending you are snogging some girl," she continued. "Well, they aren't getting off at all," added Tammy point to our latex encased groins. This brought a chorus of giggles and somehow I felt my face blush even deeper. It had been hard to start this activity but, now being forced to look into each other's eyes it was excruciating. About three minutes in the comments and instructions started. "God they look like they are enjoying it." "Stroke Stephie's hair." "Put your hand on Eric's face." "Grab Stephie's hair and pull her to you." "Squeeze Stephie's ass." It continued until finally the timer dinged. Eric and I broke eye contact immediately and I know I couldn't look at him. It was just too shameful. I couldn't believe my life had degraded to this, making out with another guy for the amusement of three evils bitches. Then the reality grabbed me that what I'd been through was just a 'warm up' as they put it that 30 minutes of lessons lay ahead. I felt a single tear roll down my cheek and was startled when I felt Eric kiss it away. I again made eye contact with him and I realized that though embarrassed on some level he was enjoying this and I have to say my despair deepened. I realized that he wasn't really in this with me like I thought he was, no he wanted to touch me and kiss me and it made the acts we had done and were about to do even more degrading somehow. "Awe isn't that cute," said Gail. "Maybe this is a bit much," said Dina. For the first time someone actually was having some sympathy for me and I had just a glimmer of hope but, it was short lived. "Oh stop, the little faggot loves this," said Gail. "Yeah, they certainly seemed to like kissing. Maybe we aren't even punishing them with this," mused Tammy. Gail reached down and reset the timer and nothing more was said though there was just a hint of concern on Dina's face as I glanced at her. The timer was started and Eric pressed his lips to mine and the instructions started. "Play with each other's nipples." "Stroke each other." "Eric suck her nipples." "Now move down to her vagina." "Stephanie play with his hair." "Eric suck her toes and lick he feet." This went on with the roles being reversed several times. Then with about 5 minutes left Gail came up with another brilliant idea. "Stephie lay down on your back. Now Eric sit on her mouth." Being made to lick another guy's ass had been humiliating but, this was hardcore eating and was taking my shame to another level. I had been forced to suck Eric's cock a lot and that was pleasant compared to this. "Now Eric grab her legs and pull them back toward you over your shoulders so you can get to here asshole too." I felt my legs being pulled up and my body being bent and then Eric's tongue on my ass. "Now sissies eat hearty," laughed Gail. I knew this was the most shameful thing I had ever done. I was eating another guy's ass. I was fucking it with my tongue and swirling it around and I felt the same being done to me. I was thankful for the morning enemas that had been added to the routine. I was shamed, debased, humiliated beyond belief, and worst of all I was starting to become aroused. I felt my traitorous member twitch and pulse and try to expand and I hate myself for it. The stimulation was just too much and then as if on queue I shuddered from the pain and pleasure denied and I felt Eric do the same. Thankfully it was about then that the timer went and we stopped this obscene act amid gales of laughter from our tormentors. This time Eric was equally shamed as we quickly stood only sharing a fleeting glance at one another before we start to dress with our backs to one another. Once we were dressed we were told to go fix our makeup and return. When we got back Gail couldn't help grill us over our reaction to the lesson and how much we liked it etc. Finally, after about 10 minutes of this she allowed us to go on with household tasks. The dinner was much the same and when we were finally sent to bed we were remind we had a 90 minute obligation 'to learning' and that they would be watching the cameras. About 40 minutes in the bedroom phone rang and Gail announced that she thought we should 'explore our feelings more deeply'. I asked what she meant and was told to put Eric on the phone. I think this was just to fuck with me and in certainly worked. "Yes?" I couldn't hear the conversation, but the look on Eric's face was enough to let me know some knew horror awaited us. I knew if he wasn't going to like it I certainly wasn't. "Come on. You can't be serious?!" Eric pleaded. "No, I don't want that. Yes, yes okay." He hung up the phone looking defeated. "She says...she says that tongues don't reach deep enough and that we should use fingers," he said dejected. It took a second for it to sink in. Was he saying...oh no she really expected us to finger fuck one another! "She said that we are continuing this session until both of us have two fingers in the other one for at least 10 minutes," he said dropping his eyes. "Oh and there is to be no lube only our saliva," he added. After we both stared at one another for a few moments and I'm sure both dwelled on the extreme humiliation of the acts we were about to perform. Finally, we moved into action and after a brief discussion we decided who was first. It was Eric who positioned himself on all fours which brought an immediate ring on the phone. After an extremely brief conversation with Gail again Eric announced that the penetrated was to lie on his back so that we could maintain eye contact throughout. I lubed my index finger as well as I could and gently as possible wormed it into his tight pucker. He grunted and made some muffled groans as I sawed it in and out trying to loosen him up for a second digit. This went on for several minutes until he said that I needed more spit. Obviously, I didn't want to reinsert my finger in my mouth so I did my best to drool as much saliva into his crack as possible. I continued the process and finally felt he was loose enough to insert the second finger. When I did me moaned and had the most pained look on his face. Once I got that second finger in I simply held them there until again the phone rang with instructions to keep them moving for the full 10 minutes. I actually felt sorry for the little prick and tried to be as gentle as possible knowing in minutes he would be doing the same to me. Eventually the phone rang again and Eric told me the message was "Time's up for round one. Change places." I assumed the position and though it went much the same Eric wasn't as gentle as I had been. I was in a fair amount of pain and the humiliation was extreme. Being on the receiving end was far worse than I anticipated. And the fact that he almost seemed to enjoy the act made it all the more embarrassing and unnerving, especially when he became erect. Like I could read the humiliation in his eyes when he was on the receiving end I could read the lust when our positions were switched. Finally after what seemed like an hour or more the phone rang and this time I answered it. "Pleasant dreams," was all that was said. The following morning I couldn't make eye contact with Eric and I had no desire to move from bed. I felt spent and used but, I finally managed to get myself up and moving after several threats by Gail. The only thing that gave me even the slightest hope was the thought that I might gain my release later in the day. Most of the day was status quo with the usual humiliations and at least Eric was on the receiving end as well. Our after meal sessions were predictably shameful but, there was no more enforced digital rectal stimulation. In fact, the session the night before was the only time we were forced to do that. Looking back on it now I can only guess that Gail figured she was breaking our will even further with that routine and I would have to say it worked. The whole day Eric and I were quiet and tame and every 'make out' training session thereafter it was always in the back of my mind. Finally, about 8:00 PM Gail announced that the girls had discussed it and they had determined that I had earned my release. I have to admit for a second that my heart leapt a little for just a second and then I thought 'What's the catch?" I was right of course there was one. I was told to strip to my bra, garter belt, and stockings and then Gail disappeared and returned when I was done with her hand behind her back. The girls were all grinning and Eric was watching with interest. Gail grinning like the Cheshire cat began "Now that my sis or should I say half sis Stephanie has served her sentence in chastity, at least for now, she has earned her release." The latex vagina was removed and I was allowed to go clean up, supervised of course so I couldn't masturbate, and then I returned to the living room where I could be the center of attention. I was positioned in the middle of the floor on my back. Gail then explained, "You have one hour to achieve as many orgasms as possible before your vagina is reattached." I was pleasantly surprised as that I would be given the chance at more than one cum considering the treatment I had been enduring. It was then I remembered that I was to be getting a punishment on Tom's behalf this evening. And my mind started to race at what was behind her back. I didn't have a long wait though. "There is of course a little catch," she said laughing. "Oh, and what might that be?" asked Dina. "Surely you remember Dina dear. I was your stipulation that he not be able to touch his little cock," laughed Gail. I was stunned trying to think how I would accomplish the deed and then envisioned it, me humping something for their amusement. "What did she have hidden behind her back?" I thought. And then it dawned on me that Gail had a slew of stuffed animals in here room and I bet I would be humping a pink hippo or a yellow bunny across the floor like some debauched cartoon character. Then she added "I think Dina envisioned you humping the floor or maybe someone's leg like a randy dog but, I don't think that is very dignified especially for a little sissy girl like you. And so.....I brought you a tool to help you get off." With a flourish she pulled the item from behind her back. For just a second my brain didn't register the item in her hand and then I realized it was something I had seen before in her beside table. It was a dildo or more accurately a vibrator. It was a black life-like penis complete with balls about 7 inches long and fairly thick. She then tossed it to me and said, "Here's the deal you use this to get off and your time starts now." I grabbed up the dildo and fumbled with it a second until it switched on and I started to rub it up and down my cock that was already almost hard. That was when she stepped over and nudged me in the nuts pretty hard with the tip of her shoe making me go limp again. "Oh no sweetie, not like that," she said wagging her finger. "Like a girl." It only took me a second to realize that she expected me to work that large hunk of latex in and out of my ass. There was no way that I would do that that, that I could do that. But, then again could I go another week. My balls were so full now I thought they were going to pop and even if I did go another week would I be given any other option. After thinking it through I moved my left hand to my mouth and used my saliva to lube my index finger and started to try to stretch myself out much as I had Eric last night. Gail stood over me grinning and the rest of the room broke out into laughter. "I can't believe this," said Eric. I glanced in his direction only to see him rubbing the front of his shorts even though his dick was restrained. I worked the one finger for a bit and then watching the timer Gail has set ticking my time away I decided I needed to move this along and after added some more spit I slid a second finger painfully in place. While working the two fingers back and forth I started to lick the dildo and get it ready. The whole time I was trying to block out that three pretty girls and one horny boy were all watching my further humiliated myself. It was a tough task though, as there were frequent comments. "Come on baby act like you like it." "Faster and deeper." "Just imagine what that cock is going to feel like." "Does that dildo remind you of your friends from the porn store?" My time was now down to 50 minutes and I made an attempt insert the black phallus. It was soon painfully obvious that I needed to first move up to three fingers as the dildo made no headway and caused considerable pain. Another 10 minutes of pain and humiliation and I had finally worked a third finger into my tight and now agonizingly stretched hole. "Awe poor baby does that hurt," laughed Gail. "I guess I was wrong from the pained look she just might be, or have been a virgin," added Tammy. Eric just stared intently with a look of lust in his eyes. After a couple more minutes I finally tried the dildo again. At first it wouldn't go and after glancing at the timer at 42 minutes I knew I had to do this now if I was ever going to get used to it in time to get off. I gritted my teeth and shoved it into me. Finally my sphincter gave a little ground and the bulbous head popped in. I jerked and made a small cry, much to the amusement of my audience, as the white pain spread for my anus to what felt like my very soul. My first instinct was to tear the thing from my ass and give up but, reason kicked in just in time and I realized that I would be in the same spot again the following week so I left the hateful thing there. Finally, after several long minutes the pain subsided and I managed to push another inch in. I then withdrew that inch and pushed it in again gaining the smallest amount of ground always stopping at the head when I withdrew. Inch by painful and humiliating inch I finally managed to have the latex cock in about half way. At that point I started working it back and forth with a little more pace and turned on vibrator. At this point Gail interjected herself again and informed me that I needed to get the whole thing in before I could turn on the vibrator. I knew as well as she did without it I would never orgasm this way. So the time read 29 minutes by the time I had the fake penis balls deep and I was allowed to flip on the vibrator again. I was before surprised and mortified that it only took about 3 minutes for me to shudder through a climax pumping the device in and out of me. Of course this brought new comments as I spilled my seed all over my belly. Strangely and disturbingly it was the most powerful orgasm of my young life. The dildo nearly slide free and I caught it at the last second and held it in place as I recovered enough to start again. "Wow she's going again I can't believe it," laughed Tammy. "Oh, come now we knew she was a slut," said Gail. My face was flushed with both shame and the after glow of my first orgasm but, I also knew that as much as I was debasing myself I better make good use of the remaining 20 minutes because who knew when I would get this chance, as twisted and degrading as it was, again. The timer read 1 minute 27 seconds when I exploded again adding my second load to the one drying on my belly. My ass was sore and my mind a little numb as spasmed through another extremely powerful orgasm. Thankfully, I was allowed to lie there and catch my breath long after the timer went off. Finally, I was able to move. "My, my, my quite the show Stephie," laugh Gail, "and such good theater." It was then that I realized she was holding the video camera. I had no idea when she had started filming but, at this point it really didn't matter they owned me. "Clean up time," Gail ordered. I started to rise, but she put her foot in my chest. "Stay there and start with your belly," she said making a scooping motion with her fingers on her own belly and then bringing them to her lips. The message was clear and the next ten minutes were spent with me cleaning my stomach a finger load at a time. During this endeavor Gail reached down and locked me back in that hateful chastity device. Once I was cleaned to her satisfaction Gail pointed to the dildo. "Lick it clean," she commanded. The relief had been much anticipated and frankly it didn't disappoint. In spite of the humiliating circumstances they were the most powerful orgasms of my life. But, the humiliation of the clean up, especially with the let down of being post-orgasm nearly outweighed it all. I felt like such a queer licking up my jism and now tasting my own ass on the dildo. Somehow, I have no way to explain it, but somehow it was worse than the things I had been forced to do with Eric. It was like sucking his dick or eating his ass but, it was ramped up a notch. My only explanation is the post-orgasm shame. "If you thought this was fun, and from your moaning and shaking I can tell you did, than next weekend when you pay Jay's penalty will be even better," Gail giggled. "I can't wait for that show!" she added. To Be Continued...